


How to Be A Heartbreaker

by Queenofhearts98fan



Category: Teen Wolf (TV)
Genre: Alive Hale Family, Alternate Universe - High School, Anal Fingering, Anal Sex, Bisexual Derek, Bottom Stiles Stilinski, Crying During Sex, Dom/sub Undertones, Drama, Emotional Hurt/Comfort, Emotional Sex, Fluff and Angst, Gay Stiles, Human Derek Hale, M/M, Past Relationship(s), Pet Names, Rimming, Romance, Rough Sex, Slow Build Derek Hale/Stiles Stilinski, Stiles Stilinski Is Bad at Feelings, Stiles Stilinski is a Little Shit, Stiles Stilinski is a Tease, Stiles is Not a Virgin, Stiles is Persistant, Stiles is a Heartbreaker, Sweet Derek, Teenager Derek, Top Derek, Top Derek Hale/Bottom Stiles Stilinski, everyone is human, stiles is a whore
Language: English
Status: In-Progress
Published: 2018-04-08
Updated: 2019-01-30
Packaged: 2019-04-20 10:19:46
Rating: Explicit
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 4
Words: 4,789
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/14258865
Author URL: https://archiveofourown.org/users/Queenofhearts98fan/pseuds/Queenofhearts98fan
Summary: Stiles is a notorious heartbreaker. He doesn't care about the feelings of other people. Whenever he gets bored with you he will dispose of you. But then a beautiful boy with jet black hair ruins the rules he had set for himself on How To Be A Heartbreaker.Based on the song How To Be A Heartbreaker by Marina and the Diamonds





	1. Prologue

**Author's Note:**

  * For [KaeLash](https://archiveofourown.org/users/KaeLash/gifts).



> Omfg this is my second story. I am so excited. I hope you all love it!

His kaleidoscope eyes bored into mine. But I will not stand down. I will not allow this man to weigh me down. I refuse.

Then the hard, cold glare turns warm and soft. The beautiful bastard had the nerve to smile at him. He shakes his head while is jet black hair flicks through the air. 

“I can't even be mad at you. I should have known this would happen.” he scoffs while he still smiles. 

Stiles scoffs back. 

“You talk as if you know me. You don't know shit about me, Derek!” he yells. 

The gorgeous man smiles again, further pissing him off. 

“See that's where you're wrong. I do know you. I think I may even know you more than you know yourself.” he says suddenly very serious. 

“Fuck you!” Stiles says. 

He then turns his back to the older male, trying to walk away from him. 

“I even know why you did what you did. You was scared.” 

Stiles stops in mid step and turns around looking at the other man in disbelief. 

“What the hell are you talking about?” Stiles questions, knowing very damn what he was playing at. 

“What I said to you last week. Those 8 letters. Those 3 words. That one sentence. It scared you. That is why we are here.” 

A lump forms in his throat at the words. Everything he said was spot on. Stiles was scared. Stiles didn't want him to say those words. 

“I can't help but feel bad for you. Whoever fucked you up really did a number on you. You are incapable of loving anyone and you want to know the saddest part? You are incapable of loving yourself.” 

For some odd reason those words hurt him. This man did know him. He was reading him like a book. But he didn't want him to know that, so he laughs it off.

“What the fuck are you talking about Derek? I love myself! You are the one with all of the internal problems!” he shouts. 

His anger instantly wavers at the last words that left his mouth. A sad and hurt look settles on the beautiful stubble clad face. His eyes look glassy. The lump in his throat continues growing as the man before him slowing started to break into pieces. His stoic expression comes through, using those fallen pieces to build a wall so Stiles couldn't see how much he hurt him.

“No. You don't…. because if you did then you wouldn't do the things you do. Because of the hatred you have for yourself and the person who did this to you, you about to lose the best thing that could've possibly happened to you. I'm so sorry that this is who you chose to be. I hope you have a happy life.” 

Derek is the one to turn his back on him. He is the one that walks away. His heart clenches at the sight. His eyes start to water and his bottom lip trembles. 

“Derek! DEREK… please don't go.” Stiles whimpers. 

But Derek didn't stop. He didn't even turn to look at him, like what is seen in the movies. When the guy walks away from the girl, while the girl calls out to the man. Then the guy turns around and looks back with his eyes filled with regret and despair. But this is not like the movies. This reality… and sometimes with reality you don't always get what you want.


	2. Rule #1: Is that you gotta have fun….

**Summary for the Chapter:**

> Stiles finds a virgin at a club and has some fun with him.

**Notes for the Chapter:**

> I have no excuse as to why it took so long for me to update. I am just a trash writer with an unforgiving life. I hope you guys enjoy my double update.

The music from the club is loud and booming through his ears. A bunch of bodies are pulsing along the erratic beat. But Stiles isn't paying attention to that. He has his eyes set on something. Someone to be more precise. The moment he came into the club he had been eyeing this man. 

As if he sensed someone was looking at him; the man looks around and his eyes settle on Stiles. A wicked smile crosses his lips as he beckons the man to come closer. He licks his lips salaciously at the brown-haired man. The man looks so flustered and if it weren't for the multicolored lights waving around the crowd, he could have sworn that the cute brunette was blushing. Said brunette starts walking toward him with a cute smile. He finally makes it to the provocative young male, wearing a sheer lacy black top with red skin-tight jeans. Stiles smirks at the man. 

“Hey there. You have a name?” Stiles says as he takes a sip of his Hennessey. 

“My name is Matt. Matt Daehler. You?” 

Stiles licks his lips again before speaking. He leans in close to his ear and grins.

“Stiles. But what I am trying to figure out is why a cutie like you is here by yourself.” He mumbles as he traces his lips along his ear.   
Matt stills and turns his face to look at Stiles.

“Stiles? As in the sheriff's son?” 

“Yup that's me. But don't pay attention that. I want to get to know you better.” Stiles says. 

Unexpectedly Stiles nibbles on his ear and smiles. Matt is stunned into silence before stammering out his answer. 

“W-well I am 18 and I like ph-photography beca-”

Stiles grabs onto Matt's crotch with a mischievous smile. Matt flinches in shock with a gasp as he looks at the freckled male. Stiles licks his lips and gives him a small squeeze causing the nervous man to moan. A smile creeps up his face like Cheshire the cat.

“I think you and I have two different definitions on getting to know each other. Why don't we talk somewhere quieter?” he says as he lets up his hand from his crotch and struts toward the club bathroom.

The nervous boy follows right behind him. Both males finally make it towards the bathroom. They enter the bathroom and Stiles closes the door and locks it. Matt looks around nervously. 

“Um, so it's very quiet here.” 

Without a word, Stiles pushes the man into one of the bathroom stalls and closes the door behind him. Matt lets out a choked off gasp in surprise. Stiles smirks before dropping down to his knees. 

“W- wait! What are you doing?” Matt asks with wide green eyes. 

Stiles merely chuckles. 

“What does it look like I'm doing? I'm about to give you a blowjob.” Stiles says as he slowly starts to unbutton Matt's jeans. 

Matt pushes Stiles's hands away from him with a huff. Stiles looks up at him with a confused expression. 

“You don't want me to?” 

“N- no I do. I mean I'm not stupid. I know what happens here. It's just that…” 

A wicked smile spreads across Stiles's face as he licks his lips and looks up at Matt.

“Are you a virgin?” he asks.

Instead of answering Matt looks everywhere other than Stiles's face.

“Awwww sweetheart. We don't have to go all the way. I can just blow you. But let me know now if you don't want to.”

A bright red blush spreads across Matt's face. 

“No… I-I want it.” he whimpers. 

Stiles licks his lips with a happy smirk. He then slowly starts to caress Matt's erection through his jeans. He feels Matt's dick twitch. He lets out a little giggle making the virgin boy feel self-conscious. Then without warning, Stiles unzips Matt's pants and pulls out his red throbbing dick. Matt gasps in surprise while Stiles wraps his hand around the base of his sex. Stiles just starts giving small kisses and licks. Matt balls up his hands at the unfamiliar sensation of someone's lips and mouth on his penis. 

“P-Please stop t-teasing me.” Matt mewls. 

Stiles lets out a dark chuckle. Then unexpectedly Stiles opens his mouth and presses his head all the way down until his nose is pressed against his pubic bone. Matt's whole body trembles. 

“O-oh my Goddd! This is so good!”

Stiles hums around his hot throbbing shaft in his mouth while tonguing the vein running down under his dick. Stiles pulls off with a wet pop. He uses his hand to jerk him off at a slow steady pace.

“Please! Please, I want more!” Matt begs while he thrusts his hips forward.

Stiles feels his own erection twitch at Matt's desperation. Stiles enjoys messing around with virgins from time to time. This time happens to be one of those times. Most virgins tend to be shy and insecure at first. But what Stiles loves the most is when virgins are stripped of their shyness and insecurity and then they give in to their primal sexual needs. He loves when they beg and plead for more, how they don't realize how slutty they become. It was so erotic to watch. 

Stiles leans back in and takes him all the way down again but this time Stiles grabs on to his ass as he bobs his head and swirls his tongue. Matt's legs were quaking as he lifts his hand off the bathroom wall and runs it through Stiles’ hair. Stiles hums around the sensitive head making the other man yelp in shock. Stiles can already taste the salty precum leaking from the tip. Stiles moans at the thought that Matt was so close.

“S-Stiles I’m c-close! Please please!” Matt rambles not even knowing what he was begging for. 

Stiles starts to bob faster and suck harder. Stiles hums again while using the leverage on Matt's ass to fuck his mouth. Matt lets out a scream right as Stiles pulls away and Matt's body stills as the hot white cum splashes across Stiles’ face. He smiles at the feel of it dripping down his face. Matt's body collapses onto the toilet as Stiles gets up and walks over to the sink and washes his face. After a long moment Matt gets out of the stall with his pants zipped up and his face flushed from embarrassment. 

“My….that was something. I-I’m sorry that I, uh, finished so quickly.” 

Stiles wipes off his now clean face. He turns and looks at Matt with a blank stare. 

“Give me your number,” Stiles demands. 

Matt's eyes widen and lists off his numbers as Stiles types it into his phone. Without a second glance, Stiles makes his way to the door before he was stopped. 

“W-wait! I was just wondering if you would like to come with me to see the mini gallery that I made.”

Stiles rolls his eyes. That is the one annoying thing about most virgins. They tend to get attached way too quickly. He turns around to face Matt with a fake smile. He walks up to him and caresses his warm cheek. 

“Awww. That is so sweet of you to ask. But no. I'll call you when I want you.” 

With that Stiles struts out of the bathroom leaving a very confused and hurt virgin to add to his lengthy list of broken spirits.


	3. Baby When You're Done You Gotta Be the First to Run

**Summary for the Chapter:**

> Stiles set his sights on the new student.

Stiles rolls his eyes for the millionth time today. He was bored and decided to text Matt and see if he can get a nice quickie before he goes home. But of course, Matt took it as an opportunity to ask him out again. So Stiles just left him on read but he couldn't take a fucking hint. At this point, it is beyond creepy and a tad bit obsessive. 

He is in the cafeteria at school with Scott eyeing him with disapproval. Stiles sighs in exasperation at his friends' judgment. 

“What, Scott? Why are you looking at me like that?” Scott raises an eyebrow with a sigh. 

“Stiles I don’t understand why you keep playing with him? Why don’t you go on a date with him? He seems nice.” 

“Scott… Honey, Baby, Sweetheart, BooBoo… we’ve been over this. Dating is not my thing. I just like to get some casual dick.” Stiles says bluntly. 

Scott makes a loud gagging noise while Stiles laughs. 

“Now you know how I feel whenever you tell me about your sexy times with Allison.” He says in between laughs. 

Scott rolls his eyes. 

“No, but all jokes aside, every guy that you talk to you don’t consider dating. It’s dangerous Stiles. One day you will end up actually loving someone and I hope for that day so you can learn what you to people.” He warns. 

Stiles lets out a loud snort. 

“That wouldn’t happen. You want to know why? Because love sucks ass.” Stiles says as he munches on a curly fry.

A lengthy silence follows between the two after that statement. Scott stares at Stiles with sad eyes. 

“Listen what that guy did to you-”

“Scott I don't want to talk about it. What's done is done.” He vehemently cuts Scott off.

“Stiles you never talk about it. You never even told me who this guy was. All I know is that he was a total asshole for doing what he did to you. Ever since that whole ordeal with this Mystery Douche you have completely changed … and not for the better might I add.” 

The very mentioning of HIM makes Stiles feel sick. It is already bad enough that he has to see this asshole on the daily basis at school but having to talk about what happened just brings back old feelings of anger and betrayal. 

“Thanks so much, Scotty but talking about it won’t do anything for me. Lunch is about to end in 5 let's get going to Mr.Harris’s before he throws a fit.” Stiles says as he readily changes the subject. 

Both boys get up from their lunch table and dump out all of their trash. They make their way down the hallway talking about rewatching Black Panther during the weekend. They make it to Chemistry just as the bell rings, signaling the start of the next period. The boys take their normal seats, Scott sitting next to Allison and Stiles sitting across from them. Mr.Harris is already in front of the class switching on the SmartBoard to show his powerpoint. Just as Mr.Harris was about to start his lecture there was a knock on the door. The teacher rolls his eyes and storms his way to the door, with every intention of yelling at the tardy student. Stiles smirks at the annoyance on the teachers face. He finally opens the door to reveal a person that made Stiles’s breath hitch in his throat. The whole class goes silent as the Mr.Harris lets the young man inside of the classroom. The young man had jet black hair, with a nicely trimmed beard. His height towering over the teacher. He had a strong build with dark and dangerous energy surrounding him. His broad shoulders are covered with black leather. When he looked amongst the class he gives a bright smile showing off his cute bunny teeth and dimples. 

“I don’t recognize you. If you are just getting to my class after all of this time then you will surely fail.” Mr.Harris says smugly.

The young man raises and intense eyebrow.

“I’m actually a new student. My name is Derek Hale. The principal said that she sent an email out to all of my teachers.” he says with an air of confidence.

Mr.Harris had a skeptical look on his face but without a word, he walks over to the computer to check his email. Stiles has his eyes glued on this new student. Stiles then turns his gaze over to Scott. The crooked jawed male meets his gaze too. The lustful look on his face tells Scott enough. Scott looks over to Derek and looks back at Stiles. Scott instantly shakes his head vigorously. 

“Don’t even think about it.” Scott mouths at him. 

Stiles merely winks at Scott and continues to leer at the sexy leather-clad male. Mr.Harris finally looks up from the computer with an embarrassed flush on his face. 

“You may have a seat now, Mr.Hale.” 

Derek walks over to an empty table next to Jared towards the back of the class. Jared’s eyes widen significantly as the attractive male sits next to him. Stiles licks his lips suggestively.

Stiles already has some dirty fantasies dancing around his head of the new student. He already has a set plan to get the boy to notice him. Based on his air of confidence, he can tell he is an alpha male. He has to be methodical when he has to lure in his next conquest. So he decides that he will play a shy and coy boy to call to his alpha male persona. 

“Mr.Stilinkski, Can you tell me where you can find the ions on the Periodic Table?” Mr.Harris’s voice bellows through his reverie. 

He looks up at Mr.Harris and answers the question correctly with an embarrassed flush. After the teacher was satisfied with the answer given, Stiles turns discretely to the back of the class to see hazel eyes staring back at him. He turns around pretending to be shy but smirks as he completed the first step to his plan of luring Derek Hale.


	4. Rule #2:  Just don't get attached to somebody you could lose.

**Summary for the Chapter:**

> Stiles goes to blow off some steam... or so he thought.

“Stiles I said forget it!. He is a brand new student and he doesn't even know about your reputation!” Scott scolds him. 

Stiles only smiles mischievously and winks. Scott shakes his head in disapproval. They are currently outside of school now since Stiles got bored and decided to ditch the rest of the day.

“That only makes it more fun that he doesn’t know. I can lure him even faster. You know that I can be very impatient.” 

“Stiles, he might also be straight. Did you think of that? No, you probably were only thinking with your second head.” Scott scolds.

But Stiles only scoffs. 

“Oh please, you act as if I have never fucked with a straight guy before. Don’t you remember I was able to pull Blake into the locker room with me? He was the biggest homophobe. All I needed was 15 minutes with him and now look he is the biggest advocate for LGBT+.” He says proudly.

“Stiles… that shouldn’t be something that you should be proud of.” He says cautiously.

“I shouldn’t be proud of what? That I completely altered an ignorant mindset of an adamant heterosexual? Scott what I did was awesome!” He boasts. 

“You know that is not what I am talking about. I’m talking about how you went about changing his mind. You blew him in the middle of the locker room! Why do you constantly want to have sex with people?”

“Scott, you of all people know that it’s more than okay to have a healthy sexual appetite.” 

“But that’s the thing, Stiles! This is not healthy! You probably had sex with almost every guy in school. You even slept with guys that had girlfriends and YOU KNEW ABOUT THEIR GIRLFRIENDS!! I have seen you at the club flirting with men who are old enough to be your father Stiles. I can’t even keep count anymore. This is very whorish behavior you might have a sex addiction. Claudia would not like the way her son turned out.” Scott says getting more passionate as he goes on. 

Stiles is used to hearing these kinds of lectures from his concerned best friend. But the mentioning of his mother is something Scott barely does. Hearing what Scott said about his mother just pissed him off.

His fists ball up in anger. Stiles snaps his fist back and aims it straight at Scott’s jaw with all of the strength he could muster up. Scott flies back and sputters in shock.

“Stiles! What the hell? Why did you just punch me?”He asks cupping his jaw as he looks at his friend with pained confusion.

“That’s for even mentioning my mother, you ass. Who knows maybe I even did you a favor. I might’ve straightened your crooked ass jaw.” He snaps.

Scott has a look of hurt all over his face but Stiles didn’t care. Scott should have known better than to even open his mouth to speak his mothers’ name. He can stay hurt for all he cares.

Stiles walks toward his Jeep and starts the car and pulls out of the parking lot like a bat out of hell.

“Who the hell does he think he is?” he mutters angrily to himself.

Stiles didn’t see the big deal of liking sex. Sex is fun and sex is great! Why is it such a bad thing to want to indulge in it? It’s not like he is actually addicted to sex. He can go for a long time without it. Plus depending on the person that Stiles tries to get with he would wait if that person didn’t want to put out just yet. If anything he enjoys when the person plays hard to get or if the person wants to have an established relationship to have sex. It makes it more fun for him when he finally gets what he wanted and then breaks things off with the person. So no he knows he definitely does not have a sex addiction because if he has to wait… he will wait for it.

Stiles let out a sigh of frustration. He needs to get his mind off of this. Stiles pulls over the side of the road and looks through his phone.

Who is Stiles’ flavor of the day? Andrew? No, he’s too small, Stiles keeps forgetting to delete his number. Corey? Definitely not! He is a power bottom like Stiles… that is not going to work! He is only fun for threesomes. Evan? Nope! He finishes too fast, he needs to be deleted too. Garry? Dammit, he is in New York! Jay? Nope, he is working! Why is it the guys that he wants to fuck are not available but the ones he doesn’t want to keep showing up on his phone. Stiles sighs again in frustration as he scrolls past all of the countless names on his phone. One name catches his eye. A part of him wants to continue scrolling past this name and look for someone else but the other part of him wants to see how far he can go with this person. After a lot of internal debating, he finally decided to give this guy a try. He texts the guy and he answers back immediately. He asks for the address and the guy gives it to him. So it’s been decided… Matt Daehler it is.

 

~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~~

Stiles rolls off of him and huffs in annoyance. 

He should have just went with his initial thought and scrolled passed Matt’s name. Hell, he should have blocked him. But no, Stiles wanted a virgin and now he is pissed off even more.

When Stiles got to Matt’s house the first thing he did was pull the shy boy in and licks and sucks on his neck. He then lets the dazed boy lead him into his bedroom and pulls the boy on top of him and started to give the boy bruising hickies. The first thing that annoyed him was that Matt kept trying to get Stiles to kiss him on the lips. He would lean in for a kiss but Stiles would turn his head so he would kiss his cheeks. The next thing that annoyed him was that he was too damn shy to return a favor after Stiles blew him within every inch of his life. But the biggest annoyance of this whole night that really put the icing on this shitty cake… was the fact the Matt wanted to bottom for his first time. Stiles kept trying to convince Matt to top him but he said he wanted to try bottoming before topping. Stiles was beyond pissed off. He is the power bottom! Why did this guy have to be a vers-bottom? Stiles would have settled if he was a vers-top. Stiles at this point is still a little horny so he wasn’t going to leave until he at least got one orgasm in. So Stiles sucked it up and topped Matt. He thought that at some point he would cum from the warmth and that he would trick himself into thinking it was a mouth on him. Matt seemed to have a great time being a pillow princess through the whole thing. Stiles was so turned off that he went from rock hard to half chub in a matter of seconds. But thank God Matt finished fast, Stiles never thought that he would be so grateful for a fast guy like Matt. So now you know how he got here, laying beside one of the biggest mistakes of his life. 

“W-wow. That was amazing! When-when I catch my breath we can definitely go again. That was… just wow.” Matt says still in his post-coital bliss.

Matt attempts to nuzzle into his chest. Stiles turns his head towards Matt with his face scrunched up in disgust.

“Who said we were going again?” Stiles snaps as he pushes Matt off of him as he gets up out of the bed completely unabashed at his nudity.

“W-Well I thought that we can go again. I had a great time with you. Maybe you can stay a little longer and we can go out to dinner.” He says nervously.

Ugh, it is already bad enough that this guy is horrible at sex now he has to deal with… feelings. Oh, fuck Stiles can feel himself getting sick at the thought of that word.

“You may have had a good time but I didn’t. I get that you are a virgin but you are shit at sex.” He says as he pulls on his briefs exasperatedly.

Matts’ eyes widened in embarrassment.

“W-What? What d-did I do wrong? I-I just need practice!” He stammers as he hurriedly crawls toward him on the bed.

“What you need is to leave me the fuck alone. Delete my number. I don’t want you calling me anymore. I thought that I could blow off some steam when I got here but if anything I am more pissed then I was before I got here.” He says finally locating his pants.

“W-Wait you only used me? You only came over here to let off steam? You actually didn’t want to see me?” 

“Was I not obvious enough for you? I constantly ignored your advances every time. I didn’t talk to you unless I wanted something from you. I was going to look past all of that shit but I can’t even stomach being in the same room with you right now.”

“Tell what I did wrong! Please, I’m sorry.” He begs, grabbing at his hand trying to pull him back into bed.

Stiles snatches his hand away and picks up his shirt to put it on. 

“You didn’t give me a blowjob after I gave you one. It is a common fucking courtesy to return a favor. I clearly told you that I am the bottom but you were so adamant to bottom for your first time. Lastly, you didn’t last long. But I guess I have to thank you for that because if I had to force myself to fuck you longer it would’ve been more hellish than it already was.” He lists off as he finds his socks and shoes and puts them on.

Matt seems to have shut down after Stiles’ scathing speech. He stares blankly at his now ruined sheets as Stiles grabs his jacket and leaves the room. Just as he thought he can make a quick getaway he hears bare feet stomping behind him.

“YOU ARE A PIECE OF SHIT!! HOW COULD YOU TREAT ME LIKE THAT?! I JUST GAVE YOU MY VIRGINITY!!” He shouts with tears welling up in his eyes.

“Well, thanks for giving it but now I don’t want it… so you can take it back.” Stiles says in a bored tone.

Matt blanches at his harsh words. Taking that as his opportunity to leave Stiles quickly runs down the stairs and out the door without a second glance. He hops in his car, starts it and takes his leave. He didn’t even make it down the street yet and his phone starts ringing. He picks it up to see Matt’s name brightening the screen. He just rolls his eyes and turns off his phone. He will just have to block his number later. Stiles is still a little annoyed with Matt and this horrible sexual experience with him but then his mind goes back to the new student. A smile spreads across his face at the thought of the sexy man.

Well, Derek will definitely make him feel better when he finally gets him into bed with him. Stiles can’t wait!


End file.
